


Burning the Midnight Oil

by prufrocknonsense



Category: Supernatural
Genre: Barebacking, Blow Jobs, Bottom Dean, Cockslut Dean, Comeplay, Desk Sex, Dom Sam, Episode: s04e17 It's a Terrible Life, Felching, Light Bondage, Light Dom/sub, Light Feminization, M/M, PWP, Sub Dean, Top Sam
Language: English
Status: Completed
Published: 2015-11-14
Updated: 2015-11-26
Packaged: 2018-05-01 15:25:13
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,016
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5210951
Author URL: https://archiveofourown.org/users/prufrocknonsense/pseuds/prufrocknonsense
Summary: <blockquote class="userstuff">
              <p>Sam Wesson and Dean Smith stay after work for some fun in Dean's office.</p>
            </blockquote>





	1. Chapter 1

If this is how they do things at Sandover, Sam Wesson is really going to like it here.

He's standing half-naked in the locked office of Mr. Dean Smith - Director of Sales and Marketing and Sam's de facto boss - leaning back just slightly against the office's sturdy desk. It's well after everyone else has gone home for the night, and Sam has no qualms about being shirtless in his workplace with his semi-hard dick sticking out of his unzipped khakis. Dean looks up at him from his equally shameless position on his knees as Sam's cock twitches against the side of his clean-shaven face.

Sam grips his fattening dick with one large hand and strokes the back of the kneeling man’s neck with the other. Dean opens his mouth hopefully as Sam slaps his cock against Dean's cheek, grinning at the desperate whine it earns him.

"You want it bad, don't you?" He asks uselessly. He can see the little aborted movements of Dean's hips, the deep breaths that make his chest expand like he's going to explode if something doesn't happen soon, and the strain of his arms pulling at the red silk tie binding them behind his back. Dean's whole body is begging for Sam's dick.

"Yes," Dean breathes. He turns his head to plant a messy kiss against the side of Sam's cock, pausing to lick the thick vein running under its surface. Sam's hand tightens its grip on the back of his neck and Dean smiles against the smooth, tight skin. Sam's eyes narrow.

"Don't be a tease, Mr. Smith."

Dean whines at the use of his formal title and spread his legs as far as they can go while still imprisoned in his constricting suit pants. Sam hadn't bothered to remove them with Dean's shirt, preferring the sight of Dean's hard cock trapped and held too tightly against his thigh by the taut material.

He re-grips his dick and guides it to his boss’ shining lips.

"Open up."

Dean obeys. His mouth drops open as Sam pulls his head forward onto his dick, stretching his jaw wide around the generous girth.

Dean gags before he can take even half of Sam's dick. Sam's guiding hand goes from firm and demanding to gentle and reassuring in seconds as Dean pulls away to cough and flex his jaw. 

"You okay?" Sam asks.

"Yeah," Dean assures him. "Been a while, is all." He licks his lips and plants them on the shiny wet head of Sam's cock once more, looking determined.

This time, he doesn't try to take more than he can. He bobs his head slowly at first, then quicker as he acclimates to the feeling of a cock in his mouth.

Apparently, cock-sucking is like riding a bike.

Sam groans above him and strokes the portion of his cock that Dean can't reach. He thrusts his hips forward only slightly, mindful of Dean's gag reflex, and traces one long finger over the droplet of sweat he finds beading on the man's temple.

"Fuck, Dean," he sighs. "How long have you been wanting this? You're so damn desperate for it, aren't you? Couldn't wait to get on your knees for me, let me tie you up and shove my cock in your mouth. Bet you can't wait for me to fuck you, right? Been thinking about that too?"

Dean whines around Sam's cock and looks up at him with shining eyes. Of course he has been.

Sam smiles down at him. "Bet it's been a long time for that, too, huh? Well, don't you worry, Mr. Smith." He pulls out of Dean's mouth again, all too pleased to see a string of drool stretch from the head of his cock to Dean's plush lips. He holds his dick still until the string breaks and a tiny dribble of saliva falls from Dean's open mouth down onto his now-wrinkled suit pants. Sam can't wait to see those pants stained with come.

"Your ass is mine tonight."

He pushes back into Dean's mouth before Dean can say anything, but the blissful look on the other man's face is enough to prove his point. Who would have thought the man was such a cockslut underneath his polished exterior?

Sam jacks his cock as Dean sucks him hungrily, wishing he could record the image of his boss' plump lips circling his dick, wet and sloppy with saliva and Sam's precome. Despite his difficulty with Sam's size, Dean knows what he's doing and it isn't long before Sam feels his balls tightening in preparation for what is shaping up to be a pretty fantastic orgasm.

"Gonna come, Dean. You want me to come in your mouth? Want to swallow what I give you like a good little slut?" Dean makes an unintelligible yet unmistakably affirmative sound around Sam's dick.

Then Sam gets an idea.

"Or," he grunts as he pushes into Dean's mouth with more force than before. "How about I come all over your pretty face?"

Dean moans and looks up at him with pleading eyes, squirming even more in his bound position, and Sam takes that as an enthusiastic yes.

He pulls out of Dean's hot, wet mouth and jacks his cock furiously in front of his face. Dean opens wide and sticks his tongue out, looking like such a shameless whore Sam can't help but come with a yell.

He strokes his cock through his orgasm, mesmerized by the way it flings ropes of come all over Dean's waiting mouth and face. It's a good thing Dean's eyes are tightly closed, because strings of it land all the way from his chin to his hairline. Sam's almost shocked by how much of it there is; it's as if his body knew to work extra hard for this image.

When he's finally done and his cock is returning to softness once more, Sam leans down to wipe the come off of Dean's closed eyelids with his thumbs. Once they're reasonably clean, Dean squints up at him and licks his lips, dragging his pink tongue through the mess there. Sam pushes his thumbs into that wet, panting mouth and groans weakly when Dean eagerly sucks them clean.

He smiles and grips Dean's shoulders, pulling him up off the floor.

Dean's legs must have been asleep, because he stumbles into Sam's firm chest immediately. He nuzzles his come-covered face into Sam's neck and breathes deeply.

"Such a good boy," Sam praises. "You were such a good boy for me, Dean. You ready for your reward?"

He doesn't wait for Dean to respond before reaching down and gripping Dean's hard cock through his obviously high-quality pants. He massages his boss' dick roughly and Dean comes surprisingly fast, almost right away.

Sam thanks the universe for blessing him with someone who gets off on giving head and being covered in come and he vows to do whatever it takes to keep him.

As Dean pants into his shoulder, Sam strokes his naked back and shushes him soothingly. He takes the opportunity to untie Dean's hands from behind his back and gently massage his wrists. When he senses Dean is coming down from his high, Sam pulls his face up so he can kiss the man's pliant lips.

They're salty from come and sweat, wet and swollen from use, and somehow the best damn thing Sam's ever tasted. Dean sighs into the kiss, allowing Sam to do whatever he wants. Sam takes his time licking into Dean's mouth and using his hands to rub most of the come off his face. Once he's satisfied with his partial cleanup job (he can't resist leaving the stuff in Dean's hair - it's just too fun to see his boss' perfect gelled part white and stiff with drying come), he turns to push Dean gently against the desk.

Dean leans back, using his arms to support himself, and smiles lazily at Sam. 

"That was fucking amazing," he says.

Sam scoffs. "You think that was it?"

Dean raises his eyebrows at him and Sam laughs.

"That was a warm-up. I'll have you bent over this desk in fifteen minutes," Sam assures him. He situates himself between Dean’s spread thighs and grins deviously. "I told you your ass is mine tonight."


	2. Chapter 2

**Summary for the Chapter:**

> Sam makes good on his promise.

**Notes for the Chapter:**

> I feel like I should warn you: this part is a bit dirtier than the last. It includes feminizing dirty talk and comeplay. The d/s vibe is also stronger. If any of that squicks you, you may want to skip it.

“Fuck, you’re hot.”

Dean is bent naked over his own desk, face hidden in his arms and legs spread wide and shameless. Sam runs his hands over the smooth expanse of his back, loving the way it dips ever so slightly to rise with the swell of Dean’s round, perky ass. God, that thing is a work of art.

Sam’s always been an ass man.

“I’m gonna fuck you right here,” he says. He is equally as naked, having divested both of them of the rest of their clothing during the fifteen minutes that separated their first orgasms of the night from now. “Right at your desk, and every time you sit in this office you’re gonna think about how I owned your ass.” Without warning, Sam spanks him, hard. Dean yelps at the sharp sting but doesn’t pull away or even turn back to look at him. Sam’s not surprised. He’s already seen the kind of man Dean is. They haven’t known each other long, but Sam already knows how to push all of Dean’s buttons.

Sam drops to his knees behind Dean’s prone form. He runs one hand over the red mark he left behind and uses the other to spread Dean's cheeks wide. He almost groans at the sight of the man’s tiny, winking hole. He had suspected that Dean was the kind of guy who shaved. Sam does appreciate a clean workspace.

He chuckles under his breath and leans in to lick a firm stripe right over Dean’s hole.

“ _Fuck,_ ” Dean gasps from above.

“That’s the plan,” Sam says as he adjusts his grip on Dean’s cheeks and buries his face in between them.

Dean jerks away in surprise but Sam holds him steady and circles his hole with his tongue. The muscle is so tight, it’ll take a lot of work to get it ready for Sam’s dick. He’s not so humble that he can’t recognize that he’s a generously endowed man.

Next, he seals his lips over Dean’s hole and sucks, earning himself a moan and another astonished “ _fuck_.”

“Like that?” Sam asks, uselessly. He wriggles his tongue against the clenched ring, pushing to get it inside. He meets resistance and doubles his efforts, using his thumbs to massage the rim while he slowly pries Dean open with his tongue.

Dean whines when Sam finally breaches him. After only a moment of having Sam’s tongue inside him, he is pushing back against Sam’s face and panting.

“Mm,” Sam hums into his crack. “Like being tongue-fucked in your office, huh? Like being eaten out like a woman?”

“Yes, fuck,” Dean whispers into the corner of his arm. Sam can’t see his face from his current position, but he would bet his life that Dean is flushed with embarrassment. He can try to hide that humiliation kink all he wants, but Sam knows it’s there.

He continues to massage the rim of Dean’s hole with his thumbs, dipping them just inside to pull gently at the first ring of muscle. He opens him up gradually, still working away with his tongue. Dean gives him the sweetest little whine when he pushes his thumbs in a little deeper, tugging him open a little farther. He spits down Dean’s crack and uses a finger to massage it into the puckered skin.

“Fuck, you’re so pretty,” Sam can’t help but remark. Dean arches his back in response, tilting his ass up a little bit more. Sam smiles. “That’s it. Show me your pussy like a good girl.”

“ _Jesus_ , Sam.”

Sam chooses to ignore him, instead bowing his head once more to lick shallowly into Dean’s hole. He brings up one long finger to press slowly inside.

“Goddamn, you’re tight. Don’t know how I’m gonna fit in here.” Sam probes his finger around a bit once it’s in to the knuckle, searching for Dean’s prostate. He hooks it a little and presses up against a soft little nub. Bingo.

Dean moans and pushes back again, begging for more. Sam bites one of his ass cheeks and applies gentle pressure to the spot, just enough to tease. Dean starts undulating his hips, fucking the air for lack of any other stimulation. Sam pushes in a second finger.

“Burns,” Dean comments.

“Mm, yeah. We’re gonna need something.”

“I have hand lotion in my middle drawer.”

“I have a better idea.”

Sam presses his fingers more insistently on Dean’s prostate, massaging and pressing on it rhythmically. He reaches his other hand around to stroke lightly over the man’s erection. He’s leaking already.

“Stop,” Dean says and reaches a hand down to grab Sam’s wrist. He finally turns to look at Sam and his face is just as flushed as Sam imagined it would be. “You’re gonna make me come.”

Sam smirks. “That’s the idea,” he says as he presses firmly down on Dean’s sweet spot.

Dean cries out and Sam cups his hand over the head of his dick to catch the ropes of come that follow. He continues to massage Dean’s insides until there’s nothing left to catch. He brings his hand back around when Dean starts to pull away from the overstimulation. His hips are still idly thrusting into nothing when Sam slicks his fingers up with his spend and presses them into his hole.

“Fuck, are you…?”

“Yep,” Sam says with a smirk. “I’m gonna fuck your own come inside you and then I’m gonna fill you up even more. Gotta get you nice and wet for me first, though.”

Dean just mumbles something incoherent into his elbow. His body has finally begun to relax, his orgasm clearly good for more than just homegrown lubricant. Sam is able to push both fingers inside of him and begin to scissor them, stretching Dean out slowly.

“That’s it. Open up for me. Gotta open up if you want my cock.”

“I’m trying!”

“I know,” Sam shushes him. “You’re doing so well, baby. Letting me in so nice.” He crooks his fingers a little, brushing up against Dean’s prostate again. Dean jumps.

“Too sensitive?” Sam asks.

“A little. I like it though.”

“Knew you would.”

Sam adds a third finger, first swirling it around Dean’s rim and adding more of his come to ease the way. It goes in easier.

“You ready?” He asks, still pushing his fingers in and out rhythmically.

Dean hums. “Yeah, think so.”

“Good.” Sam pulls his fingers free and stands. He uses the rest of the come in his hand to slick up his cock, mixing it with the pre-come already gathering at his tip.

Sam lines himself up behind Dean, admiring the way his body is now covered lightly in sweat. Dean's back muscles twitch, probably from being bent over for so long, and the little bow in his legs looks all the more inviting from this angle.

“You have a perfect ass, you know that?”

Dean just wiggles it enticingly, pressing back onto Sam’s cock. Sam presses his dick in between those firm, round cheeks and thrusts a few times, using his hands to squeeze them together around him.

“Could just fuck you like this. Could just fuck your crack and come all over your back. You’d let me, wouldn’t you? All that prep would be for nothing, but you’d let me.”

“Please. Please don’t.”

“Oh? You’d rather I fuck you? Fill you up with my cock and pound you against your desk like a whore?”

“God, yes.”

“Ask me nicely.”

“Please?”

Sam shakes his head and slaps Dean’s ass. “Not good enough. _Really_ ask me to fuck you. Tell me exactly how you want to be fucked and then _beg_ me to do it.”

“Fuck,” Dean groans. “Please fuck me. Want you to fuck me so bad.”

“Better. Give me more.”

“Want you to fuck me hard, pound me against my desk, fuckin’ destroy me,” Dean pleads. His voice has gone high and thin, desperate and needy. “Want to be stuffed full of you, wanna feel you inside me. Wanna get fucked so hard it hurts tomorrow. Wanted it from the moment I saw you. Fuck, _please_ , just give it to me.”

Sam smiles, overwhelmingly pleased. “Very good,” he says as he runs his fingers through Dean’s hair with one hand and lines his cock up with Dean’s hole with the other.

The push in is slick but slow-going. Sam watches as the tip of his cock breaches Dean’s body, popping inside and stretching his rim wide open. Dean grunts and Sam places a hand at the back of his neck as he pushes in, kneading out the tension there.

Dean lets out a litany of whispered profanity as Sam continues his slide into him. Distantly, Sam remembers what Dean said about it having been a long time since he’d sucked cock. His assumption had been that it had been a long time since he’d last done this, too. Dean is clearly eager for it, but Sam doesn’t want to push him before he’s had time to properly get back in the saddle, so to speak.

Sam reaches down to fondle Dean’s cock as he pushes in the last couple inches. It’s mostly limp, spent from its two previous orgasms, but Sam has a feeling he can get one more out of Dean before the night is through. He begins to lightly stroke it to half-mast before making his first slow thrusts in.

Dean whines and pushes back onto Sam’s cock, impatient and unsatisfied. Sam just laughs.

“I know you’re hungry for it, baby, but you gotta let me take care of you. Promise I’ll give you what you need.”

Sam grinds his hips in circles and increases the speed of his thrusts. He gets up to a decent pace, paying close attention to Dean’s reactions. His cock is still valiantly struggling to fill completely and his mouth is open and gasping against his arm, so Sam takes those as his cues to keep going.

He grips Dean’s hips tightly and pistons inside of him harder. Dean lets out little grunts on each push in, somewhere between pain and pleasure.

“God, you’re tight,” Sam remarks. He slides his hands from Dean’s hips up to his ass, gripping his cheeks so he can watch Dean’s tiny hole take his cock. The rim is stretched wide, red and shiny with come and sweat. “Look at you. Fuckin’ natural. Take dick so well, baby.”

He releases Dean’s ass so he can re-grip his hips and tug him back on his cock. Dean’s fingers scrabble at the desk as he’s pulled roughly onto Sam’s dick, looking for something to hold onto to counterbalance Sam's fierce thrusts. Sam groans and fucks him harder.

“You love this, don’t you? Love being owned. Fucked like a whore, used like a sex toy. So damn hungry for it, must have been craving this for a long time, huh?”

“Yes, fuck, yes.” Dean is barely holding himself up anymore, just letting Sam use his body as he pleases. All of the tightly held poise and dignity of Mr. Dean Smith is totally stripped away. His pathetic whines as he’s fucked and filled with cock are the sounds of nothing but a desperate slut.

Grunting, Sam presses Dean’s body against the desk, holding him down and dominating him completely as he fucks him so hard his own hips start to feel sore. He digs his short nails into Dean’s hip with one hand and uses the other to shove the man’s face against the surface of the desk. He wants to keep talking, wants to call Dean all manner of degrading, filthy things, but it feels like the air has been punched out of him and all he can do is continue the brutal motion of his hips as he chases his second orgasm of the night.

He comes with a shout, shoving in as deep as possible to empty his balls inside Dean’s overworked body. He pulls out just before the last pulse of come is pulled from his body, holding his cock just against Dean’s hole to let the remainder of his spend shoot directly over the red, raw skin. Sam groans as he watches the poor, used muscle attempt to close even as more come slides out.

He takes Dean’s hands in his and pulls his arms back. Dean lays there pliantly as Sam makes him grip his own ass cheeks and spread them wide to show off the mess Sam made of his hole.

“Stay,” Sam commands. Dean gives him a sleepy sigh in response, holding his position obediently. Sam smiles and drops to his knees behind the man once more.

“Look at you,” he says, mostly to himself. “Stuffed full of come, letting it trickle out of you like a filthy slut. Goddamn.” He leans in and licks the dribble of come out of Dean’s crack and moans. He takes advantage of the lingering looseness and stuffs two fingers inside, shoveling out a generous dollop and licking them clean.

“Oh, God,” Dean whimpers and squirms. “Sam.”

Sam runs his hands down Dean’s trembling thighs and hushes him. “Gotta get you all cleaned up, baby.”

He seals his mouth over Dean’s hole once more and sucks, using his tongue to scoop out more of the warm, smooth come. The outer ring twitches and he can feel Dean’s inner muscles contracting as he lets out a steady stream of soft moans and whispered profanity.

Sam reaches around to grip Dean’s cock, figuring he’s had enough time to be ready to come again, but instead of the leaking erection Sam had expected to find, his cock is entirely soft. The filthy pleasure of the night is marred by the worry that Dean had lost his erection until Sam’s hand drifts up towards his belly and slides through a cooling slickness there.

“When did you come?” Sam asks, devilishly calm. His hand swirls around in the mess on Dean’s belly, rubbing it into his skin idly. “When I was fucking you or when I was sucking the come out of your filthy cunt?”

“ _Sam_ ,” Dean groans and shakes his head.

“Tell me.”

“When you were…” Dean trails off, shoulders tense and hunched. “When you were eating me out.”

“You came untouched, Dean. That was very, very good,” Sam praises. He stands up and drapes himself over Dean’s body, kissing the back of his neck and licking up the beads of sweat that have gathered there. “I didn’t even have to tell you to.”

Dean shrugs beneath him. “It kinda took me by surprise. I wasn’t expecting you to do…all that.”

Sam straightens up and pulls Dean with him. Dean grunts at the position change and Sam wraps him in his arms, using his thumbs to massage his sore lower back. “It was good, though, right?”

“Fuck, do you have to ask? Nobody’s ever done this kind of shit to me,” Dean mumbles into the crook of Sam’s neck. His voice is quiet and slightly muffled, panting hot breaths against Sam’s already heated skin. “I like what you to do to me. I love it.”

Sam grips him tighter and kisses his sweaty temple. He cradles Dean’s face in his hands and looks into his eyes, seeing traces of embarrassment and leftover lust. Mostly, though, is the dreamy look of post-sex tranquility that Sam knows very well.

“You did so well,” he says, not allowing Dean to look away from him as he says it. “You’ve made me so happy tonight, Dean. I’m proud of you.”

He can see the wetness in Dean’s eyes, tears too tiny to fall, but just enough to confirm everything Sam needed to know.

A part of Dean needs this, and Sam is more than happy to be the person to give it to him.

**Notes for the Chapter:**

> Let me know what you think, please! And I'm really starting to like this as a 'verse, so there may be more to come if people continue to be interested in it.


End file.
